EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

2-oxobutyric acid
2-ketobutanoic acid

Sponsors

Name:2-oxobutanoic acid
CAS Number: 600-18-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-986-9
FDA UNII:B92RB6HY1A
Nikkaji Web:J2.726J
Beilstein Number:1700514
MDL:MFCD00004164
XlogP3-AA:0.10 (est)
Molecular Weight:102.08942000
Formula:C4 H6 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:589 2-oxobutyric acid
FLAVIS Number:08.066 (Old)
DG SANTE Food Flavourings:08.066 2-oxobutyric acid
FEMA Number:3723 2-oxobutyric acid
FDA Mainterm: ALPHA-KETOBUTYRIC ACID
 
Physical Properties:
Appearance:white clear liquid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 32.00 to 34.00 °C. @ 760.00 mm Hg
Boiling Point: 80.00 to 82.00 °C. @ 16.00 mm Hg
Vapor Pressure:0.482000 mm/Hg @ 25.00 °C. (est)
Flash Point: 179.00 °F. TCC ( 81.67 °C. )
logP (o/w): -0.731 (est)
Soluble in:
 alcohol
 water
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Type: caramellic
Odor Strength:high ,
recommend smelling in a 1.00 % solution or less
sweet brown caramellic creamy lactonic
Odor Description:at 1.00 % in propylene glycol. sweet brown caramel creamy lactonic
sweet brown caramellic creamy lactonic
Odor Description:Sweet, brown, caramellic, creamy with lactonic nuances
Mosciano, Gerard P&F 18, No. 3, 53, (1993)
Flavor Type: brown
sweet brown creamy caramellic fatty
Taste Description: at 25.00 ppm. Sweet, brown, creamy, caramellic with a fatty nuance
Mosciano, Gerard P&F 18, No. 3, 53, (1993)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
2-oxoButyric Acid
CFC Scientific
2-oxoButyric Acid, 97 %
EMD Millipore
For experimental / research use only.
2-oxoButyric Acid
Jiangyin Healthway
2-Ketobutyric acid
New functional food ingredients
Jiangyin Healthway
2-Oxobutyric acid
M&U International
2-oxoBUTYRIC ACID, Kosher
Penta International
2-OXOBUTYRIC ACID, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
2-oxoButyric Acid ≥97%
Sigma-Aldrich
2-Oxobutyric acid, ≥95%, FG
Odor: caramel; creamy
Certified Food Grade Products
Synerzine
2-ketobutyric Acid
also named 2-Ketobutyric Acid
TCI AMERICA
For experimental / research use only.
2-oxobutyric acid >98.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.024 (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 13
 average usual ppmaverage maximum ppm
baked goods: -2.00000
beverages(nonalcoholic): -1.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -12.00000
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
 
Safety References:
European Food Safety Athority(efsa):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf
Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):600-18-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :58
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-oxobutanoic acid
Chemidplus:0000600180
 
References:
 2-oxobutanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:600-18-0
Pubchem (cid):58
Pubchem (sid):135018017
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C00109
HMDB (The Human Metabolome Database):HMDB00005
FooDB:FDB003359
YMDB (Yeast Metabolome Database):YMDB00071
Export Tariff Code:2915.60.0000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
FAO:2-Oxobutyric acid
 
Potential Blenders and core components note
For Odor
acidic
cyclohexyl acetic acid
FL/FR
aldehydic
acetyl nonyryl
FL/FR
balsamic
2-
acetyl furan
FL/FR
buttery
acetoin
FL/FR
acetyl butyryl
FL/FR
acetyl isobutyryl
FL/FR
acetyl propionyl
FL/FR
butyl butyryl lactate
FL/FR
3,4-
hexane dione
FL/FR
caramellic
caramel pentadione
FL/FR
cyclotene
FL/FR
cyclotene hydrate
FL/FR
alpha,alpha-
dimethyl anisyl acetone
FL/FR
ethyl 2-hydroxy-2-methyl butyrate
FL/FR
ethyl cyclopentenolone
FL/FR
ethyl maltol
FL/FR
5-
ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-one
FL/FR
fenugreek absolute
FL/FR
geranyl crotonate
FR
immortelle absolute
FL/FR
levulinic acid
FL/FR
maltol
FL/FR
maltyl propionate
FL/FR
maple furanone
FL/FR
menthone lactone
FL/FR
mesitene lactone
FR
5-
methyl furfural
FL/FR
rosefuran
FL/FR
shoyu furanone
FL/FR
strawberry furanone
FL/FR
strawberry furanone acetate
FL/FR
toffee furanone
FL/FR
cheesy
butyric acid
FL/FR
coconut
coconut decanone methyl
FR
delta-
decalactone
FL/FR
delta-2-
dodecenolactone
FL/FR
gamma-
heptalactone
FL/FR
delta-
nonalactone
FL/FR
gamma-
octalactone
FL/FR
delta-
undecalactone
FL/FR
coumarinic
phthalide
FL/FR
tonka bean resinoid
FR
creamy
butyl lactate
FL/FR
gamma-
butyrolactone
FL/FR
creamy lactone
FL/FR
3-
heptyl dihydro-5-methyl-2(3H)-furanone
FL/FR
para-
vanillic acid
FL/FR
para-
vanillyl alcohol
FL/FR
earthy
1-
nonen-3-ol
FL/FR
ethereal
ethyl 4-pentenoate
FL/FR
ethyl pyruvate
FL/FR
iso
valeraldehyde propylene glycol acetal
FL/FR
fatty
(Z)-
dairy lactone
FL/FR
ethyl undecylenate
FL/FR
4-
methyl octanoic acid
FL/FR
fermented
butyl laevo-lactate
FL/FR
ethyl (E)-2-crotonate
FL/FR
floral
iso
jasmone
FL/FR
methyl dihydrojasmonate
FL/FR
fruity
acetoin acetate
FL/FR
gamma-
decalactone
FL/FR
epsilon-
dodecalactone
FL/FR
(E)-
ethyl tiglate
FL/FR
farnesyl acetone
FL/FR
methyl (Z)-5-octenoate
FL/FR
tetrahydrofurfuryl acetate
FL/FR
gamma-
undecalactone (aldehyde C-14 (so-called))
FL/FR
green
iso
amyl 3-(2-furan) propionate
FL/FR
iso
butyl benzyl carbinol
FL/FR
(Z)-4-
hepten-1-ol
FL/FR
(Z)-4-
heptenal
FL/FR
(Z)-4-
heptenal diethyl acetal
FL/FR
2-
heptyl furan
FL/FR
herbal
butyl levulinate
FL/FR
mushroom
3-
octen-2-ol
FL/FR
musty
3-
acetyl-2,5-dimethyl furan
FL/FR
nutty
2-
acetyl-3,5(or 6)-dimethyl pyrazine
FL/FR
2,3-
dimethyl pyrazine
FL/FR
nutty cyclohexenone
FL/FR
phenolic
4-
methyl-2,6-dimethoxyphenol
FL/FR
spicy
(E)-
coconut decanone ethyl
FR
(E)-
tiglic acid
FL/FR
sweet
vanilla oleoresin bali
FL/FR
tonka
6-
amyl-alpha-pyrone
FL/FR
mint lactone
FL/FR
octahydrocoumarin
FL/FR
tonka bean absolute
FR
vanilla
ortho-
dimethyl hydroquinone
FL/FR
ethyl vanillin
FL/FR
ethyl vanillin isobutyrate
FL/FR
ethyl vanillin propylene glycol acetal
FL/FR
vanillin
FL/FR
vanillyl acetate
FL/FR
vanillyl isobutyrate
FL/FR
vanillylidene acetone
FL/FR
vegetable
methional
FL/FR
tetrahydrofurfuryl alcohol
FL/FR
waxy
allyl nonanoate
FL/FR
ethyl palmitate
FL/FR
methyl laurate
FL/FR
2-
nonanol
FL/FR
octyl 2-methyl butyrate
FL/FR
octyl isobutyrate
FL/FR
delta-
tetradecalactone
FL/FR
undecanoic acid
FL/FR
For Flavor
No flavor group found for these
2-
acetyl-3,4,5,6-tetrahydropyridine
FL
allyl 2-furoate
FL
allyl methyl trisulfide
FL
benzyl disulfide
FL
6-
decenoic acid
FL
2,5-
diethyl tetrahydrofuran
FL
alpha,alpha-
dimethyl anisyl acetone
FL/FR
ortho-
dimethyl hydroquinone
FL/FR
epsilon-
dodecalactone
FL/FR
delta-2-
dodecenolactone
FL/FR
ethyl 2-hydroxy-2-methyl butyrate
FL/FR
ethyl 4-pentenoate
FL/FR
5-
ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-one
FL/FR
farnesyl acetone
FL/FR
furfuryl acetone
FL
heptanal 2,3-butane diol acetal
FL
mango furanone
FL
massoia bark oil
FL
menthone lactone
FL/FR
rosefuran
FL/FR
(R)-
tonka furanone
FL
iso
amyl 3-(2-furan) propionate
FL/FR
acidic
acidic
levulinic acid
FL/FR
dextro,laevo-
tartaric acid
FL
aldehydic
acetyl nonyryl
FL/FR
amber
iso
butyl benzyl carbinol
FL/FR
balsamic
vanillylidene acetone
FL/FR
brown
5-
methyl furfural
FL/FR
tetrahydrofurfuryl acetate
FL/FR
(E)-
tiglic acid
FL/FR
burnt
furfuryl alcohol
FL
buttery
butyl laevo-lactate
FL/FR
diacetyl
FL
3,4-
hexane dione
FL/FR
cabbage
methyl 2-thiofuroate
FL
caramellic
caramel furanone
FL
caramel malted mambo flavor
FL
caramel pentadione
FL/FR
creme brulee flavor
FL
cyclotene
FL/FR
cyclotene hydrate
FL/FR
ethyl maltol
FL/FR
5-
ethyl-3,4,5,6-tetramethyl cyclohexen-2-one
FL
fenugreek absolute
FL/FR
barley
malt extract
FL
maltol
FL/FR
maltyl propionate
FL/FR
maple cream flavor
FL
maple furanone
FL/FR
3-
methyl butyl 2-furyl butyrate
FL
shoyu furanone
FL/FR
strawberry furanone
FL/FR
strawberry furanone acetate
FL/FR
toffee furanone
FL/FR
coconut
delta-
decalactone
FL/FR
(R)-
massoia lactone
FL
6-
methyl coumarin
FL
octahydrocoumarin
FL/FR
coffee
coffee creme brulee flavor
FL
2-
thiophene thiol
FL
coumarinic
phthalide
FL/FR
creamy
acetoin
FL/FR
acetyl butyryl
FL/FR
acetyl isobutyryl
FL/FR
6-
amyl-alpha-pyrone
FL/FR
butyl butyryl lactate
FL/FR
creamy lactone
FL/FR
mint lactone
FL/FR
delta-
nonalactone
FL/FR
octyl isobutyrate
FL/FR
delta-
undecalactone
FL/FR
gamma-
undecalactone (aldehyde C-14 (so-called))
FL/FR
para-
vanillic acid
FL/FR
para-
vanillyl alcohol
FL/FR
dairy
butyl lactate
FL/FR
creme brulle coffee flavor
FL
methyl (Z)-5-octenoate
FL/FR
earthy
1-
nonen-3-ol
FL/FR
eggy
egg nog creme brulee flavor
FL
fatty
(Z)-
dairy lactone
FL/FR
ethyl undecylenate
FL/FR
2-
heptyl furan
FL/FR
4-
methyl octanoic acid
FL/FR
2,4-
octadien-1-ol
FL
(E,E)-2,4-
undecadienal
FL
2,4-
undecadienal
FL
floral
methyl dihydrojasmonate
FL/FR
fruity
acetoin acetate
FL/FR
acetyl isovaleryl
FL
gamma-
decalactone
FL/FR
(E)-
ethyl tiglate
FL/FR
furfuryl valerate
FL
3-
heptyl dihydro-5-methyl-2(3H)-furanone
FL/FR
2-
pentanoyl furan
FL
iso
valeraldehyde propylene glycol acetal
FL/FR
green
(Z)-4-
hepten-1-ol
FL/FR
(Z)-4-
heptenal
FL/FR
(Z)-4-
heptenal diethyl acetal
FL/FR
immortelle absolute
FL/FR
iso
jasmone
FL/FR
herbal
butyl levulinate
FL/FR
5-
hydroxymethyl furfural
FL
jammy
ethyl cyclopentenolone
FL/FR
lactonic
gamma-
heptalactone
FL/FR
gamma-
octalactone
FL/FR
milky
gamma-
butyrolactone
FL/FR
mushroom
3-
octen-2-ol
FL/FR
musty
ethyl (E)-2-crotonate
FL/FR
nutty
2-
acetyl furan
FL/FR
3-
acetyl-2,5-dimethyl furan
FL/FR
2-
acetyl-3,5(or 6)-dimethyl pyrazine
FL/FR
2,3-
dimethyl pyrazine
FL/FR
nutty cyclohexenone
FL/FR
peanut oxazole
FL
tetrahydrofurfuryl alcohol
FL/FR
phenolic
4-
methyl-2,6-dimethoxyphenol
FL/FR
rummy
ethyl pyruvate
FL/FR
sour
butyric acid
FL/FR
spicy
benzylidene acetone
FL
sweet
caramel dione
FL
cyclohexyl acetic acid
FL/FR
dextro-
sorbitol
FL
vanilla oleoresin bali
FL/FR
toasted
acetyl propionyl
FL/FR
tomato
methional
FL/FR
vanilla
ethyl vanillin
FL/FR
ethyl vanillin isobutyrate
FL/FR
ethyl vanillin propylene glycol acetal
FL/FR
vanillin
FL/FR
vanillyl acetate
FL/FR
vanillyl isobutyrate
FL/FR
waxy
allyl nonanoate
FL/FR
ethyl palmitate
FL/FR
furfuryl octanoate
FL
methyl laurate
FL/FR
2-
nonanol
FL/FR
octyl 2-furoate
FL
octyl 2-methyl butyrate
FL/FR
delta-
tetradecalactone
FL/FR
undecanoic acid
FL/FR
 
Potential Uses:
FLbutterscotch
FLcaramel
FLsugar brown
 
Occurrence (nature, food, other):note
 beer
Search PMC Picture
 
Synonyms:
2-ketobutanoic acid
2-oxobutanoic acid
2-oxo-butanoic acid
 butanoic acid, 2-oxo-
a-ketobutric acid
2-ketobutyric acid
2-keto-N-butyric acid
2-oxo-butyric acid
2-oxo-n-butyric acid
a-ketobutyric acid
a-keto-n-butyric acid
a-oxobutyric acid
a-oxo-n-butyric acid
alpha-ketobutyric acid
alpha-oxo-N-butyric acid
 butyric acid, 2-oxo-
2-oxobutyricacid
a-ketobutyricacid
 formic acid, propionyl-
3-methyl pyruvic acid
 methyl-pyruvic acid
3-methylpyruvic acid
 propionyl formic acid
 propionylformic acid
 pyruvic acid, methyl-
 

Articles:

PubMed:[Screening and identification of an endophytic bacterium with 1-aminocyclopropane-1-carboxylate deaminase activity from Panax ginseng and its effect on host growth].
PubMed:Gordonibacter urolithinfaciens sp. nov., a urolithin-producing bacterium isolated from the human gut.
PubMed:Crystal structures of human CtBP in complex with substrate MTOB reveal active site features useful for inhibitor design.
PubMed:A QM/MM study on the reaction pathway leading to 2-aceto-2-hydroxybutyrate in the catalytic cycle of AHAS.
PubMed:Molecular evolution of threonine dehydratase in bacteria.
PubMed:A one-pot system for production of L-2-aminobutyric acid from L-threonine by L-threonine deaminase and a NADH-regeneration system based on L-leucine dehydrogenase and formate dehydrogenase.
PubMed:Highly stereoselective biosynthesis of (R)-α-hydroxy carboxylic acids through rationally re-designed mutation of D-lactate dehydrogenase.
PubMed:Conserved pyridoxal protein that regulates Ile and Val metabolism.
PubMed:Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures.
PubMed:C-terminal binding proteins are essential pro-survival factors that undergo caspase-dependent downregulation during neuronal apoptosis.
PubMed:Enhancing (L)-isoleucine production by thrABC overexpression combined with alaT deletion in Corynebacterium glutamicum.
PubMed:BRCA1 expression is epigenetically repressed in sporadic ovarian cancer cells by overexpression of C-terminal binding protein 2.
PubMed:Determination of α-keto acids in pork meat and Iberian ham via tandem mass spectrometry.
PubMed:Synergy as design principle for metabolic engineering of 1-propanol production in Escherichia coli.
PubMed:Microbial Community-Level Physiological Profiles (CLPP) and herbicide mineralization potential in groundwater affected by agricultural land use.
PubMed:Efficient bioconversion of l-threonine to 2-oxobutyrate using whole cells of Pseudomonas stutzeri SDM.
PubMed:Isolation of Rhizobacteria from Jatropha curcas and characterization of produced ACC deaminase.
PubMed:Variability of Escherichia coli O157 strain survival in manure-amended soil in relation to strain origin, virulence profile, and carbon nutrition profile.
PubMed:Effects of gamma-ray-induced free radicals on the metal content and amino acid composition of human metallothionein-1.
PubMed:Asymmetric formal [3+2] cycloaddition reaction of isocyanoesters to 2-oxobutenoate esters by a multifunctional chiral silver catalyst.
PubMed:Kinetic resolution of 2-hydroxybutanoate racemic mixtures by NAD-independent L-lactate dehydrogenase.
PubMed:Mechanistic studies of 1-aminocyclopropane-1-carboxylate deaminase: characterization of an unusual pyridoxal 5'-phosphate-dependent reaction.
PubMed:Biosynthesis of chiral 3-hydroxyvalerate from single propionate-unrelated carbon sources in metabolically engineered E. coli.
PubMed:Three-component assembly and divergent ring-expansion cascades of functionalized 2-iminooxetanes.
PubMed:Therapeutic targeting of C-terminal binding protein in human cancer.
PubMed:Cloning and characterisation of a cystathionine β/γ-lyase from two Oenococcus oeni oenological strains.
PubMed:Exploring methionine γ-lyase structure-function relationship via microspectrophotometry and X-ray crystallography.
PubMed:Expanding metabolism for total biosynthesis of the nonnatural amino acid L-homoalanine.
PubMed:Characterization of ACC deaminase gene in Pseudomonas entomophila strain PS-PJH isolated from the rhizosphere soil.
PubMed:Efficient production of 2-oxobutyrate from 2-hydroxybutyrate by using whole cells of Pseudomonas stutzeri strain SDM.
PubMed:Site-directed mutagenesis on human cystathionine-gamma-lyase reveals insights into the modulation of H2S production.
PubMed:Transaminase-catalyzed asymmetric synthesis of L-2-aminobutyric acid from achiral reactants.
PubMed:Acetohydroxyacid synthase, a novel target for improvement of L-lysine production by Corynebacterium glutamicum.
PubMed:Directed evolution of Methanococcus jannaschii citramalate synthase for biosynthesis of 1-propanol and 1-butanol by Escherichia coli.
PubMed:Identification of a methioninase inhibitor, myrsinoic acid B, from Myrsine seguinii Lév., and its inhibitory activities.
PubMed:Direct methods and residue type specific isotope labeling in NMR structure determination and model-driven sequential assignment.
PubMed:Isothermal titration microcalorimetry reveals the cooperative and noncompetitive nature of inhibition of Sinorhizobium meliloti L5-30 dihydrodipicolinate synthase by (S)-lysine.
PubMed:[Overproduction of noncanonical amino acids by Escherichia coli cells].
PubMed:Elucidation of an alternate isoleucine biosynthesis pathway in Geobacter sulfurreducens.
PubMed:Production of the apoptotic cellular mediator 4-Methylthio-2-oxobutyric acid by using an enzymatic stirred tank reactor with in situ product removal.
PubMed:SanM catalyzes the formation of 4-pyridyl-2-oxo-4-hydroxyisovalerate in nikkomycin biosynthesis by interacting with SanN.
PubMed:Perspectives of bacterial ACC deaminase in phytoremediation.
PubMed:A novel strategy for enzymatic synthesis of 4-hydroxyisoleucine: identification of an enzyme possessing HMKP (4-hydroxy-3-methyl-2-keto-pentanoate) aldolase activity.
PubMed:The crystal structure of Escherichia coli TdcF, a member of the highly conserved YjgF/YER057c/UK114 family.
PubMed:Bacillus decisifrondis sp. nov., isolated from soil underlying decaying leaf foliage.
PubMed:Enzymology and evolution of the pyruvate pathway to 2-oxobutyrate in Methanocaldococcus jannaschii.
PubMed:Silencing threonine deaminase and JAR4 in Nicotiana attenuata impairs jasmonic acid-isoleucine-mediated defenses against Manduca sexta.
PubMed:Evidence for distinct L-methionine catabolic pathways in the yeast Geotrichum candidum and the bacterium Brevibacterium linens.
PubMed:Accumulation of homolanthionine and activation of a novel pathway for isoleucine biosynthesis in Corynebacterium glutamicum McbR deletion strains.
PubMed:Functional analysis of all aminotransferase proteins inferred from the genome sequence of Corynebacterium glutamicum.
PubMed:Crystallization and some properties of D-lactate dehydrogenase from Staphylococcus sp. LDH-1.
PubMed:Involvement of a branched-chain aminotransferase in production of volatile sulfur compounds in Yarrowia lipolytica.
PubMed:The mitochondrial branched-chain aminotransferase (AtBCAT-1) is capable to initiate degradation of leucine, isoleucine and valine in almost all tissues in Arabidopsis thaliana.
PubMed:Structural analysis of Pseudomonas 1-aminocyclopropane-1-carboxylate deaminase complexes: insight into the mechanism of a unique pyridoxal-5'-phosphate dependent cyclopropane ring-opening reaction.
PubMed:Transcarboxylase 5S structures: assembly and catalytic mechanism of a multienzyme complex subunit.
PubMed:Assay method for antitumor L-methionine gamma-lyase: comprehensive kinetic analysis of the complex reaction with L-methionine.
PubMed:Role of a conserved arginine in the mechanism of acetohydroxyacid synthase: catalysis of condensation with a specific ketoacid substrate.
PubMed:Reduced transaminase B (IlvE) activity caused by the lack of yjgF is dependent on the status of threonine deaminase (IlvA) in Salmonella enterica serovar Typhimurium.
PubMed:Effect of alpha-ketobutyrate on microvascular thickness in the diabetic rat kidney.
PubMed:Catabolism of volatile sulfur compounds precursors by Brevibacterium linens and Geotrichum candidum, two microorganisms of the cheese ecosystem.
PubMed:Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene.
PubMed:Dual influence of the carbon source and L-methionine on the synthesis of sulphur compounds in the cheese-ripening yeast Geotrichum candidum.
PubMed:A sensitive and robust method for obtaining intermolecular NOEs between side chains in large protein complexes.
PubMed:Reaction of 1-amino-2-methylenecyclopropane-1-carboxylate with 1-aminocyclopropane-1-carboxylate deaminase: analysis and mechanistic implications.
PubMed:Amino acid catabolism and generation of volatiles by lactic acid bacteria.
PubMed:Substrate recognition by 2-oxoacid:ferredoxin oxidoreductase from Sulfolobus sp. strain 7.
PubMed:Synthesis of labeled 1-amino-2-methylenecyclopropane-1-carboxylic acid, an inactivator of 1-aminocyclopropane-1-carboxylate deaminase.
PubMed:Sulfur compound production by Geotrichum candidum from L-methionine: importance of the transamination step.
PubMed:Contribution of enzymic alpha, gamma-elimination reaction in detoxification pathway of selenomethionine in mouse liver.
PubMed:The large scale synthesis of "unnatural" amino acids.
PubMed:Conversion of Escherichia coli pyruvate oxidase to an 'alpha-ketobutyrate oxidase'.
PubMed:Biochemical and molecular characterization of taurine:pyruvate aminotransferase from the anaerobe Bilophila wadsworthia.
PubMed:L-Vinylglycine is an alternative substrate as well as a mechanism-based inhibitor of 1-aminocyclopropane-1-carboxylate synthase.
PubMed:Metabolic and K(ATP) channel-independent actions of keto acid initiators of insulin secretion.
PubMed:Engineering of a novel biochemical pathway for the biosynthesis of L-2-aminobutyric acid in Escherichia coli K12.
PubMed:Artefactual pyruvate and 2-oxobutyrate produced by trimethylsilylation of methylmalonic and ethylmalonic acids in the presence of oxygen.
PubMed:Metabolic engineering of Arabidopsis and Brassica for poly(3-hydroxybutyrate-co-3-hydroxyvalerate) copolymer production.
PubMed:Description of Cellulophaga baltica gen. nov., sp. nov. and Cellulophaga fucicola gen. nov., sp. nov. and reclassification of [Cytophaga] lytica to Cellulophaga lytica gen. nov., comb. nov.
PubMed:Use of 13C nuclear magnetic resonance and gas chromatography to examine methionine catabolism by lactococci.
PubMed:Substrate selectivity and biochemical properties of 4-hydroxy-2-keto-pentanoic acid aldolase from Escherichia coli.
PubMed:Pyruvate protects neurons against hydrogen peroxide-induced toxicity.
PubMed:Active site plasticity in D-amino acid oxidase: a crystallographic analysis.
PubMed:Oocyte and zygote ketoaldehyde utilisation.
PubMed:High resolution 1H NMR investigations of the reactivities of alpha-keto acid anions with hydrogen peroxide.
PubMed:Production of heteropolymeric polyhydroxyalkanoate in Escherichia coli from a single carbon source.
PubMed:Determination of short-chain aliphatic, oxo- and hydroxy-acids in drinking water at low microgram per liter concentrations.
PubMed:Metabolic effects of inhibitors of two enzymes of the branched-chain amino acid pathway in Salmonella typhimurium.
PubMed:The effect of three alpha-keto acids on 3-mercaptopyruvate sulfurtransferase activity.
PubMed:In vivo threonine oxidation rate is dependent on threonine dietary supply in growing pigs fed low to adequate levels.
PubMed:A spectrophotometric determination of alpha-dicarbonyl compounds and its application to the enzymatic formation of alpha-ketobutyrate.
PubMed:Channeling behavior and activity models for Escherichia coli K-12 acetohydroxy acid synthases at physiological substrate levels.
PubMed:Threonine dehydratases of Corynebacterium glutamicum with altered allosteric control: their generation and biochemical and structural analysis.
PubMed:Methionine transamination--metabolic function and subcellular compartmentation.
PubMed:Threonine 246 at the active site of the L-lactate dehydrogenase of Bacillus stearothermophilus is important for catalysis but not for substrate binding.
PubMed:The oxygenase reaction of acetolactate synthase.
PubMed:Cofactor identification of threonine-serine dehydratase from sheep liver.
PubMed:Acetohydroxy acid synthase and threonine deaminase activities, and the biosynthesis of isoleucine-leucine-valine in Streptococcus bovis.
PubMed:Alpha-keto acids are novel siderophores in the genera Proteus, Providencia, and Morganella and are produced by amino acid deaminases.
PubMed:A mechanism for valine-resistant growth of Escherichia coli K-12 supported by the valine-sensitive acetohydroxy acid synthase IV activity from ilvJ662.
PubMed:Eurystatins A and B, new prolyl endopeptidase inhibitors. II. Physico-chemical properties and structure determination.
PubMed:In vivo nephrotoxic action of an isomeric mixture of S-(1-phenyl-2-hydroxyethyl)glutathione and S-(2-phenyl-2-hydroxyethyl)glutathione in Fischer-344 rats.
PubMed:Physiological implications of the substrate specificities of acetohydroxy acid synthases from varied organisms.
PubMed:Leaky pantothenate and thiamin mutations of Salmonella typhimurium conferring suphometuron methyl sensitivity.
PubMed:Pleiotropic effects of poxA regulatory mutations of Escherichia coli and Salmonella typhimurium, mutations conferring sulfometuron methyl and alpha-ketobutyrate hypersensitivity.
PubMed:Effects of alpha-ketobutyrate and alpha-hydroxybutyrate on the enzymatic determination of acetoacetate and beta-hydroxybutyrate.
PubMed:Physiological implications of the specificity of acetohydroxy acid synthase isozymes of enteric bacteria.
PubMed:Involvement of ack-pta operon products in alpha-ketobutyrate metabolism by Salmonella typhimurium.
PubMed:Toxic accumulation of alpha-ketobutyrate caused by inhibition of the branched-chain amino acid biosynthetic enzyme acetolactate synthase in Salmonella typhimurium.
PubMed:A method for simultaneous determination of the two possible products of acetohydroxy acid synthase.
PubMed:Methionine metabolism in isolated perfused livers from rats fed on zinc-deficient and restricted diets.
PubMed:Effect of alpha-ketobutyrate on palmitic acid and pyruvate metabolism in isolated rat hepatocytes.
PubMed:Effects of organic acids on the synthesis of citrulline by intact rat liver mitochondria.
PubMed:The occurrence of 4-methylthio-2-hydroxybutyrate in human urine.
PubMed:Sensitivity of a Salmonella typhimurium aspC mutant to sulfometuron methyl, a potent inhibitor of acetolactate synthase II.
PubMed:High performance liquid chromatography determination of cystathionase activity in human and rabbit lenses.
PubMed:p-Cresol formation by cell-free extracts of Clostridium difficile.
PubMed:alpha-Ketobutyrate metabolism in perfused rat liver: regulation of alpha-ketobutyrate decarboxylation and effects of alpha-ketobutyrate on pyruvate dehydrogenase.
PubMed:Directed biosynthesis of paulomycin A. The effect of L-methionine, L-threonine and alpha-ketobutyric acid.
PubMed:Heat-shock treatment lethal for mammalian cells deprived of glucose and glutamine: protection by alpha-keto acids.
PubMed:Biochemical oxygen activation as the basis for the physiological action of tetrachlorodecaoxide (TCDO).
PubMed:Defect in alpha-ketobutyrate metabolism: a new inborn error.
PubMed:[Kinetics of uptake of Pherajod by the rabbit eye].
PubMed:Biochemical model reactions for cataract research.
PubMed:[The uptake of potassium iodide and its effect as an antioxidant in isolated rabbit eyes].
PubMed:In vivo study of LDH isoenzyme activities in heart, liver and testis cytosols of gossypol-treated rats.
PubMed:Synthesis of the isoleucyl- and valyl-tRNA synthetases and the isoleucine-valine biosynthetic enzymes in a threonine deaminase regulatory mutant of Escherichia coli K-12.
PubMed:Characterization of alpha-ketobutyrate metabolism in rat tissues: effects of dietary protein and fasting.
PubMed:Transaminase inhibitors block glycolysis and G1 to S phase progression in chick embryo fibroblasts: reversal by alpha-keto acids.
PubMed:Metabolic alterations mediated by 2-ketobutyrate in Escherichia coli K12.
PubMed:Role of 2-ketobutyrate as an alarmone in E. coli K12: inhibition of adenylate cyclase activity mediated by the phosphoenolpyruvate: glycose phosphotransferase transport system.
PubMed:Mycoplanecins, novel antimycobacterial antibiotics from Actinoplanes awajinensis subsp. mycoplanecinus subsp. nov. III. Structural determination of mycoplanecin A.
PubMed:The structure of the abortive nicotinamide adenine dinucleotide-pyruvate-lactate dehydrogenase complex as determined by circular dichroism.
PubMed:2-Ketobutyrate: a putative alarmone of Escherichia coli.
PubMed:Metabolic basis for the isoleucine, pantothenate or methionine requirement of ilvG strains of Salmonella typhimurium.
PubMed:Effect of pyruvate and its analogs on the thiamine pyrophosphate binding in the active center of muscle pyruvate dehydrogenase.
PubMed:Acetohydroxy acid synthase isoenzymes of Escherichia coli K12 and Salmonella typhimurium.
PubMed:Mechanistic studies on the pyridoxal phosphate enzyme 1-aminocyclopropane-1-carboxylate deaminase from Pseudomonas sp.
PubMed:Conversion of alpha-ketobutyrate to alpha-amino-n-butyric acid by isolated rat liver cells: effect of ethanol.
PubMed:A role for threonine deaminase in the regulation of alpha-acetolactate biosynthesis in Escherichia coli K12.
PubMed:Properties of alpha-hydroxyacid dehydrogenase isozymes from Trypanosoma cruzi.
PubMed:Decrease of intracellular cystine content in cystinotic fibroblasts by inhibitors of gamma-glutamyl transpeptidase.
PubMed:[Estimation of serine- and threonine dehydratase activity of blood serum].
PubMed:A sensitive determination of alpha-keto acids by gas-liquid chromatography and its application to the assay of L-glutamate dehydrogenase and aminotransferases.
PubMed:Hydroxyamino acid utilization and alpha-ketobutyrate toxicity in Pseudomonas cepacia.
PubMed:Substrate channeling: alpha-ketobutyrate inhibition of acetohydroxy acid synthase in Salmonella typhimurium.
PubMed:Beta-hydroxy-alpha-ketobutyric acid in Drosophila melanogaster, with reference to biosynthesis of drosopterins.
PubMed:Stereochemistry of the conversions of L-threonine and D-threonine into 2-oxobutanoate by the L-threonine and D-threonine dehydratases of Serratia marcescens.
PubMed:Serine sensitivity of Escherichia coli K 12: partial characterization of a serine resistnat mutant that is extremely sensitive to 2-ketobutyrate.
PubMed:[Oxidative deamination of beta-methylaspartic acid].
PubMed:Inactivation of the pyruvate dehydrogenase component from pigeon breast muscle pyruvate dehydrogenase complex by alpha-ketobutyric acid.
PubMed:Methionine degradation by Pseudomonas fluorescens UK1 and its methionine-utilizing mutant.
PubMed:High-speed liquid chromatographic determination of phenylpyruvic acid.
PubMed:Sheep liver serine-threonine dehydratase. I. Purification and evidence for covalently linked alpha-ketobutyrate as its cofactor.
PubMed:The formation of 2-hydroxybutyric acid in experimental animals.
PubMed:beta-Decarboxylation of L-aspartic acid: a metal chelate-catalyzed reaction.
PubMed:Neuropharmacological comparison of cystathionine, cysteine, homoserine and alpha-ketobutyric acid in cats.
PubMed:A comparative study of the ability of methionine or linolenic acid to act as precursors of ethylene in plant tissues.
PubMed:Biosynthesis of ethylene. 4-methylmercapto-2-oxobutyric acid: an intermediate in the formation from methionine.
PubMed:On the mechanism of sensitivity to leucine in the case of "leucine sensitive hypoglycemia". II. The hypoglycemic affect of alpha-ketobutyric acid in the case of "leucine sensitive hypoglycemia".
PubMed:2-Oxobutyric acid: effects of its condensation products on lactate dehydrogenase activity.
PubMed:Effect of alpha-ketobutyric acid on exytetracycline production in serine-containing medium.
PubMed:Alpha-keto acids in vitamin-free casein hydrolyzates (acid).
PubMed:Effects of certain thiamine analogs on the enzymatic decarboxylation of alpha-ketobutyric acid.
PubMed:alpha-Ketobutyric acid as a product in the enzymatic cleavage of cystathionine.
PubMed:Pyruvate oxidation in brain: Evidence derived from the metabolism of alpha-ketobutyric acid.
 
Notes:
Flavour ingredient 2-Ketobutyric acid is a substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid is a product of the lysis of cystathionine. It is also one of the degradation products of threonine. It can be converted to propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted to succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle.; Alpha-ketobutyric acid is a product of the lysis of cystathionine.; It is also one of the degradation products of threonine.
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